Can anyone fix this city?

For more than two hours on a Tuesday evening, in a modern extension to a historic Presbyterian church in the affluent Pacific Heights neighbourhood, the candidates for San Francisco’s mayor parade in front of a microphone. They are here for a showcase hosted by the local Junior League and, one by one, the four Democrats leading the race address the trio of concerns that dominate public conversation in the city: homelessness, car theft and the lack of affordable housing.

City supervisor Jane Kim’s legal training has enabled her to shine at these events, with speeches that amount to a machine-gun barrage of statistics simultaneously demonstrating passion and intellectual authority. Tonight, however, 39-year-old Kim goes uncharacteristically silent when a moderator asks her to name one decision she made that didn’t go to plan. Kim fiddles about briefly before addressing an issue she would rather not discuss. “The policy I get criticised the most for is the Mid-Market Tax Exclusion,” she says. “Also known as the ‘Twitter Tax Break’.”

Back in 2011, San Francisco offered Twitter a deal: if the company established its HQ in a long-vacant Market Street building it would be exempt from six years of payroll taxes on any new jobs created at the site. The social-media company has since become one of the city’s largest employers and Uber, Pinterest, Dropbox and Airbnb soon moved in next door. The neighbourhood was transformed and its change soon reflected in rising rents. Kim, who sponsored the tax break, is often forced to defend her role.

Long the most politically progressive big city in the US, San Francisco is now its wealthiest and its most unequal. An unexpected special election to choose a new mayor in June has abruptly thrust the city’s residents into a referendum on who, if anyone, is responsible for the city’s stratospheric growth.

As such, the biggest challenge for all four of the leading candidates – along with Kim, career politicians London Breed, Mark Leno and Angela Alioto – is channelling the dissatisfaction that’s rife among an electorate unwilling to accept unchecked growth. “People are against the status quo,” says Dan Newman, a strategist for former state senator Leno. “There are Teslas driving by construction rigs, and tents on the street.”

The last time San Francisco had a wide-open election for mayor was in 2003. Then, voters were forced to consider what kind of leadership would best serve a proud city adjusting to gradual decline. Following the 2000 dotcom crash, many feared it was doomed to the fate of a tourism economy.

Since then, the city has added 100,000 new residents and a rapid injection of wealth beyond the civic imagination. The city’s two mayors over the past 15 years positioned themselves as business-friendly. Yet economic growth arrived thanks to factors largely beyond their control, not least venture-capital-fuelled investment in technology firms eager to set up shop downtown rather than in Silicon Valley suburbs. One quarter of the city’s 16 top employers today didn’t even exist in 2003. The largest of them, Salesforce, has just erected the tallest tower on the city’s already monumental skyline. Unemployment stands at 2.3 per cent, the lowest ever recorded.

Yet none of the four leading candidates is inclined to celebrate any part of the boom, let alone take credit for it. “Tech came to town without a plan,” says Alioto at her law office. It’s festooned with mementos from decades serving in, and running for, city office; the 68-year-old daughter of a former mayor is running for a third time. “Who’s paying for the infrastructure that is going to support 3,000 new people on one block? Nobody planned anything.”

The man who should shoulder at least some of that blame is not in a position to defend himself. On 11 December 2017, mayor Ed Lee collapsed in a supermarket near his home and was declared dead hours later. The 65-year-old had been an accidental executive himself. In 2010, Gavin Newsom, first elected mayor in 2003, ascended to California’s lieutenant governorship. San Francisco’s board of supervisors tapped Lee, a soft-spoken city administrator, to complete the rest of Newsom’s term.

Lee’s steady hand and consensus politics impressed local business titans, who – along with Chinese-American community leaders excited to see the first of their own as mayor – launched a very public “Run, Ed, Run!” pressure campaign. In late 2011 he comfortably won his own full term; in 2015 he won again without serious opposition.

When Lee died, the president of the board of supervisors automatically moved into his office on an interim basis. Charismatic 43-year-old London Breed sparkled in ways that Lee did not, and had an inspiring story of overcoming hardship after growing up in public housing. But political jockeying and concern over her supposed unfair advantage in the upcoming special election meant that, after one month as acting mayor, Breed’s colleagues abruptly replaced her with venture capitalist Mark Farrell.

Lee’s death created a void in more than just executive leadership; the leading candidates have all framed their critique of the city’s current era with barely a mention of the man who presided over it. There is particular concern that any remark that could be interpreted as a personal slight towards Lee would raise hackles within a Chinese-American community that represents about one-fifth of San Francisco’s electorate. “There is indeed great deference to his memory,” says Leno. “That’s the nature of losing an elected leader.” He’s sitting in his campaign headquarters blocks from the Castro District printing shop he opened 40 years ago. The 66-year-old candidate’s greatest asset – and liability – may be a conciliatory bonhomie that makes him wary of pointing fingers.

Even unspoken, Lee’s legacy permeates the race: the lack of affordable housing dominates discussion. The debate has revolved around a legislative proposal by Scott Wiener, a Democratic state senator whose district includes San Francisco. Senate Bill 827 would require cities in California to permit construction of buildings up to five storeys around train and ferry stations, and along busy bus lines. The proposed law would open up significant patches to much denser development than communities had been heretofore willing to permit. “We decided there’s something sacred about local control and we’re going to let existing residents decide whether to let anyone else in,” says Wiener, blaming it for the state’s limited supply. “I knew it would be controversial.”

That was especially true in San Francisco, where estimates suggest more than 90 per cent of blocks would be covered by the new, looser rules. Voters can stand near a subway station, look around in every direction and imagine how the vistas would be broken with five-storey condominiums on every corner.

“We’d be running roughshod over the character of our city to house employees who may or may not be here in five years,” says Alioto. “This is going to make our city like Hong Kong, 10 storeys high on every block. That is what Hong Kong is, that’s not what San Francisco is.”

In fact, Breed is the only one of the candidates to back Wiener’s bill. It is a distinction that her opponents hope will emphasise the caricature they paint of her as a pawn of downtown business interests primed to extend Lee’s laissez-faire attitude towards growth. (The endorsement of Breed by Ron Conway, a technology investor who is known as a city hall power broker, doesn’t help her cause.)

By spring, Kim’s campaign found that voters knew plenty about Wiener’s bill. Often referring to it by its official name, sb827, they were asking volunteers about her views on it. Debates on sb827 suited Kim’s strategy as a left-wing firebrand endorsed by Bernie Sanders. John Golinger, her campaign manager, printed flyers that highlighted Kim’s opposition – “We don’t have to destroy our neighbourhoods to save San Francisco” – and distributed them across the city. “It’s about how we decide what gets built and who decides,” says Golinger.

Just after midday one Sunday in spring, Breed arrives in Bayview, a largely African-American neighbourhood, for the opening of a campaign office. It is a beautiful day and she is encouraging a festival vibe. Bayview is not in her district but her campaign treats it as home turf. “Don’t go anywhere if you like good ribs,” she tells the crowd. “After we finish this, we’re throwing down in the office.”

That morning she had received the endorsement of the San Francisco Chronicle, the city’s leading newspaper and a reliable bulwark for business-friendly opinion against left-wing excess. “Breed has been most pronounced in acknowledging that the affordable housing problem is not going to be cured by city hall mandates alone,” the paper’s editorial board noted, applauding her support for Wiener’s bill.

Breed, however, makes no mention of the endorsement as she jovially speaks to supporters in Bayview. At every opportunity she emphasises that she is a renter and a “native San Franciscan” – a way of setting herself apart from the tech-sector arrivistes (and from Kim, who was raised in New York). She also wants to make the terms of Farrell’s putsch a campaign issue. “When they tell us to sit down we’re going to stand up even taller,” she says. It is a message Breed hopes will resonate not only with African-American voters but also women, who will identify with how the city’s foremost female elected official saw her dream job yanked from her.

Identity rumbles beneath the surface of a race that’s largely about quality-of-life issues, with every candidate trying to claim a historic purpose to his or her campaign. Breed would be the city’s first African-American woman to serve as mayor; Kim the first Asian-American woman. Leno would be the first openly gay mayor. Even Alioto has a claim: “I would be the first father-daughter. I’m also the first Sicilian.”

But as election day nears, the momentous challenge facing the winning candidate becomes all the more apparent. After all, it’s very likely that the runners-up will start preparing for a rematch in the regularly scheduled November 2019 election. “The fact is,” says Golinger, “whoever wins has to govern for a year and a half.”

After more than a decade of transformation, it won’t be enough time to address the myriad issues that San Francisco faces. But the new mayor might just have enough time to figure out what the city wants to become and, perhaps, a vision of how it might get there.